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Synthesis 2014; 46(12): 1630-1638
DOI: 10.1055/s-0033-1341044
DOI: 10.1055/s-0033-1341044
paper
Inter- and Intramolecular [4+2]-Cycloaddition Reactions with 4,4-Disubstituted N-Silyl-1,4-dihydropyridines as Precursors for N-Protonated 2-Azabutadiene Intermediates
Further Information
Publication History
Received: 24 January 2014
Accepted after revision: 27 February 2014
Publication Date:
01 April 2014 (online)
Abstract
An efficient and straightforward method for the synthesis of polycyclic ring systems with a central 2-azabicyclo[2.2.2]octane unit is developed. The process is based on [4+2]-cycloaddition reactions that are performed with N-protonated 2-azabutadiene intermediates as heterodienes, generated from 4,4-disubstituted N-silyl 1,4-dihydropyridines. As dienophiles, cyclopentadiene for the intermolecular cycloaddition and an allyl moiety already attached to the 4,4-disubstituted 1,4-dihydropyridines for the intramolecular variant, are used.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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